Methanol → Diisopropyl Ether

HRID 2237734Notes

Reaction equation

HRID 2237734 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][C@H:8]([CH:22]([CH3:24])[CH3:23])[CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@@H:11]2[CH2:13][O:12]2)=[CH:5][C:4]=1[O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32].[N-:33]=[N+:34]=[N-:35].[Na+].[Cl-].[NH4+].[CH3:39]O>>[N:33]([CH2:13][C@@H:11]([C@@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:9][C@H:8]([CH2:7][C:6]1[CH:25]=[CH:26][C:3]([O:2][CH3:1])=[C:4]([O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32])[CH:5]=1)[CH:22]([CH3:24])[CH3:23])[OH:12])=[N+:34]=[N-:35].[CH:28]([O:27][CH:4]([CH3:3])[CH3:5])([CH3:29])[CH3:39]

Participants

6

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 59849018HCID 59849018, compound

Product 2

HCID 7914Diisopropyl EtherHCID 86613532HCID 86613532, compound

Procedure

The solution of 3.10 g of tert-butyl {3(S)-[4-methoxy-3-(3-methoxypropoxy)benzyl]4-methyl-1(S)-(R)-oxiranylpentyl}carbamate (Example 1b) in 64 ml of methanol is admixed with 1.04 g of sodium azide and 0.62 g of ammonium chloride and stirred at reflux over 6 hours. The reaction solution is cooled, poured onto ice-water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed successively with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) and subsequent crystallization (diisopropyl ether) as white crystals. Rf=0.29 (1:2 EtOAc-heptane); Rt=21.60 (gradient II). m.p. 98-99° C.

Workup

  1. temperatureat reflux over 6 hours
  2. temperatureThe reaction solution is cooled
  3. additionpoured onto ice-water
  4. extractionextracted with tert-butyl methyl ether (2×)
  5. washThe combined organic phases are washed successively with water and brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-8941c8c2b88c4f6eb095941fa3f1c512
Source dataset
uspto-grants-2010_05
Patent number
US07718675B2

Reaction notes

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